Boston is a city with a very rich history and is filled with tons of culture. After all, it’s known as one of the country’s oldest cities and happens to be the capital of Massachusetts. Some notable historical events include the Boston Tea Party, the Battle of Bunker Hill, as well as the Siege of Boston. With all that history, it makes for a great place to live and/or visit. Even more so around a special day like Valentine’s Day!


Enjoy Valentine’s Day Dinner on Boston Harbor

Couple eating dessert with rose petals on table.

Treat your special Valentine to something extraordinary on Valentine’s Day. City Cruises Boston has the perfect romantic outing, where you can kick back and relax on a luxurious yacht. The Boston Valentine’s Day Signature Dinner Cruise is a wonderful way to show your Valentine all the romance you can fit into an evening cruise around Boston Harbor. It is two glorious hours on the water, so be sure to dress in your semi-formal attire and get ready for an amazing Valentine’s dinner you will never forget.

This exhilarating evening on the water will include dancing to the music from a live DJ, delectable and creative cocktails available from the cash bar, and a chef-designed signature buffet menu along with Boston’s breathtaking views. You will be greeted by warm, welcoming, and hospitable staff who will ensure you have an amazing time.

The buffet menu includes Caesar Salad and Caprese Salad. Main courses feature Coriander Crusted Salmon and Root Vegetable Fricassee, while Garlic Mashed Potatoes and Seasonal Vegetables complement your main course. Enjoy cakes, brownies, and seasonal fruit for dessert. Unlimited coffee, tea, and iced tea are available as well as a guaranteed table for your party.


The cruise has extras and upgrades available for a more customized experience. Available packages include:

Silver Package:cheering champagne

  • Glass of champagne/sparkling wine
  • Single rose, per couple

Gold Package:

  • Glass of champagne/sparkling wine
  • Single rose, per couple
  • Guaranteed window seat

Platinum Package:

  • Romance package (bottle of Mumm [or equivalent], 1/2 dozen roses and logoed flutes)
  • Guaranteed window seat


Fun Things to Do in Boston on Valentine’s Day

This Valentine’s Day, Feb. 14, 2024 from 6:30pm to 8:00pm, head over to Trillium Brewing Co. for “Valentines Day (*couples only*). Not your average paint night! #Pour Art“, led by local artist Rahim Gray who will teach couples how to create their own abstract masterpiece. He will discuss paint pouring techniques, intricacies of color behavior, as well as tips and tricks on mixing paint. Pour Art is creating a painting without a paintbrush. You and your significant other will enjoy this not-so-typical paint workshop, and tickets will include everything you will need to create your own masterpiece.

For something a little different on Valentine’s Day, bring your special someone, or even a friend or bunch of friends to “Valentine’s Day: Stories from the Stage ‘Smitten’ live taping (in-person)“. It will be at GBH Studios on Feb. 14, 2024, from 6:30pm to 9:00pm. You will spend an evening enjoying “stories inspired by love and on the theme of smitten,” according to, while enjoying craft cocktails and local treats. “Enjoy both heartfelt and hilarious stories of love. From massive crushes and platonic love to the nearly perfect — and the perfectly disastrous — these storytellers cover it all.”

Prior to Valentine’s Day get your cupcakes ready and head over to Ashland Public Library on Feb. 6, 2024 for “Decorating Cupcakes for Gal/Pal/Valentine’s Day *For Adults“ from 6:00pm to 7:00pm. This is the perfect way to “up your game” when it comes to decorating cupcakes. It will feature cake artist Dawn Rice Norton who will offer tips on professional decorating. She will also share cupcake and fondant recipes and talk cupcake decorating. Registration is required and opens on Jan. 23, 2024. Materials will be supplied.


valentines decor


Other Unique Valentine’s Day Options in Boston

Bring your date for a night of ice skating at The Boston Common Frog Pond. Whether you are a longtime ice skater or a beginner, this is a great place to enjoy Valentine’s Day. You can try skating lessons here, including private or group lessons. Skates and lockers are available to rent. Hang tightly onto your partner as you glide across the ice. Later you can head over to the Frog Pond Café, which has sandwiches, salads, snacks, and beverages. Ice skating runs from November to March.

Get romantic at Carrie Nation Restaurant and Cocktail Club, a speakeasy in downtown Boston that is sure to make your Valentine’s Day just a bit spicey for you and your date. Here you will find yourself feeling like you are back in the 1920s during the time of prohibition. They have various food menus as well as cocktails to quench your desire for a drink in a bygone era. “And though the main dining spaces are charming and inviting, slip along the bar to a corridor just beyond, making your way to the red velvet curtain and get ready to get raided,” according to their website. “Make sure to have a twenty spot, secret handshake or password and find yourself in Boston’s Original Speakeasy.”


Multiple colorful cocktails on a bar


Book Your Boston Valentine’s Day with City Cruises

Boston is such a great town with so much to do, it’s easy to see how it’s a top Valentine’s Day destination. Even with all there is to do, nothing beats a day on the water. So, book your Valentine’s Day with City Cruises in Boston and you won’t go wrong. You and your Valentine won’t want to miss the romance on the water.